Abstract: Philosophy is an historical product, which is definitively consolidated with Plato and Aristotle. As it constitutes a novelty within the polis, it is not just regarded with suspicion from its very beginning, but it is also the target of severe criticism. Those who are dedicated to philosophy are stigmatized as odd people, as it is shown by many classical texts. Regarding to his thought and his practical proposal, the Academic gave continuity to philosopher’s crazy image. However, he did so in an ironic way. He suggested that philosopher’s strangeness is not due to a real deviation from the behaviour that by nature is most suitable for humans, but the opposite, i.e. caused by the wrong opinions of those who are not philosophers. In fact, apart from well defining which is philosophy’s nature, one of the most urgent tasks that Plato has to deal with in his dialogues is to make a defence of philosophy as the best way of life, depicting it as the most sensible and according to nature.